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Strain and Hückel Aromaticity: Driving Forces for a Promising New Generation of Electron Acceptors in Organic Electronics

Authors

  • F. G. Brunetti Dr.,

    1. Materials Research Laboratory, University of California Department of Chemistry and Biochemistry, Santa Barbara, CA 93106 (USA), Fax: (+1) 805-893-4120
    2. Center for Polymers and Organic Solids, University of California, Santa Barbara, CA 93106 (USA)
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  • X. Gong Dr.,

    1. Center for Polymers and Organic Solids, University of California, Santa Barbara, CA 93106 (USA)
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  • M. Tong Dr.,

    1. Center for Polymers and Organic Solids, University of California, Santa Barbara, CA 93106 (USA)
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  • A. J. Heeger Prof.,

    1. Center for Polymers and Organic Solids, University of California, Santa Barbara, CA 93106 (USA)
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  • Fred Wudl Prof.

    1. Materials Research Laboratory, University of California Department of Chemistry and Biochemistry, Santa Barbara, CA 93106 (USA), Fax: (+1) 805-893-4120
    2. Center for Polymers and Organic Solids, University of California, Santa Barbara, CA 93106 (USA)
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  • We are grateful to The University of California, Santa Barbara MRL for financial support through seed project N4SEWF and to Konanka Technologies Inc. Technical assistance from Dr. J. Pavlovich for the mass spectroscopy and G. Wu for the crystal structure is also acknowledged.

Abstract

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Straining at the leash: The main features of electron-accepting materials with a 9,9′-bifluorenylidene backbone are strain relief and a gain in aromaticity. These dimers (see picture) exhibit absorption near the red spectral region (ca. 600 nm) and HOMO (5.58–5.06 eV) and LUMO (3.37–3.09 eV) energy levels, which, together with high solubility and thermal stability render these materials attractive acceptors for bulk heterojunction (BHJ) solar cells.

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